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Chemical Compound Review

phosphocitrate     2-phosphonooxypropane-1,2,3- tricarboxylic...

Synonyms: AG-E-79041, KST-1B2444, AC1Q6RUM, CTK1A4419, AR-1B5247, ...
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Disease relevance of phosphocitrate


High impact information on phosphocitrate


Biological context of phosphocitrate

  • This paper reports the synthesis of phosphocitric acid via the phosphorylation of triethyl citrate with o-phenylene phosphochloridate, hydrogenolysis of the product to yield triethyl phosphocitrate, hydrolytic removal of the blocking ethyl groups and also chromatographic purification [10].
  • We found that basic calcium phosphate (BCP) crystals greatly stimulated the endocytotic activity of cells by rendering the cells more permeable and that the anti-calcification agent phosphocitrate and several others inhibited the crystals-mediated endocytosis [11].
  • The adsorption of citrate and phosphocitrate ions by hydroxyapatite (HAP) surfaces and their influence on the constant composition growth kinetics of HAP have been investigated [12].

Anatomical context of phosphocitrate


Associations of phosphocitrate with other chemical compounds


Gene context of phosphocitrate

  • METHOD: Using a semi-quantitative reverse transcription-polymerase chain reaction method and phosphocitrate (PC), a specific inhibitor of the biological effects of BCP crystals, we examined the effects of BCP on the steady state transcript levels of metalloproteinase (MMP)-1, -3, -9 and -13 and TIMP-1 and -2 in human fibroblasts [20].
  • PC, at 10(-3) mol/L, inhibited the TGF-beta 1-induced proliferation of MPA and 3T3 cells, but had no effect on normal fibroblasts [4].

Analytical, diagnostic and therapeutic context of phosphocitrate


  1. Phosphocitrate inhibits mitochondrial and cytosolic accumulation of calcium in kidney cells in vivo. Tew, W.P., Malis, C.D., Howard, J.E., Lehninger, A.L. Proc. Natl. Acad. Sci. U.S.A. (1981) [Pubmed]
  2. Phosphocitrate blocks calcification-induced articular joint degeneration in a guinea pig model. Cheung, H.S., Sallis, J.D., Demadis, K.D., Wierzbicki, A. Arthritis Rheum. (2006) [Pubmed]
  3. Atherogenesis. Mitigation of monocyte adhesion to arterial endothelium in hyperlipidemic rats by phosphocitrate, a phosphorylated polycarboxylic acid. Shankar, R., Tuyethong, N., Sallis, J.D. Atherosclerosis (1986) [Pubmed]
  4. Fibroblasts from mice with progessive ankylosis proliferate excessively in response to transforming growth factor-beta 1. Krug, H.E. J. Investig. Med. (1998) [Pubmed]
  5. Inhibitors of articular calcium crystal formation. Sallis, J.D., Cheung, H.S. Current opinion in rheumatology. (2003) [Pubmed]
  6. Basic calcium phosphate crystal-induced prostaglandin E2 production in human fibroblasts: role of cyclooxygenase 1, cyclooxygenase 2, and interleukin-1beta. Morgan, M.P., Whelan, L.C., Sallis, J.D., McCarthy, C.J., Fitzgerald, D.J., McCarthy, G.M. Arthritis Rheum. (2004) [Pubmed]
  7. Phosphocitrate inhibits a basic calcium phosphate and calcium pyrophosphate dihydrate crystal-induced mitogen-activated protein kinase cascade signal transduction pathway. Nair, D., Misra, R.P., Sallis, J.D., Cheung, H.S. J. Biol. Chem. (1997) [Pubmed]
  8. Inhibition of calcium pyrophosphate dihydrate crystal formation in articular cartilage vesicles and cartilage by phosphocitrate. Cheung, H.S., Kurup, I.V., Sallis, J.D., Ryan, L.M. J. Biol. Chem. (1996) [Pubmed]
  9. Phosphocitrate prevents disease progression in murine progressive ankylosis. Krug, H.E., Mahowald, M.L., Halverson, P.B., Sallis, J.D., Cheung, H.S. Arthritis Rheum. (1993) [Pubmed]
  10. Synthesis and characterization of phosphocitric acid, a potent inhibitor of hydroxylapatite crystal growth. Tew, W.P., Mahle, C., Benavides, J., Howard, J.E., Lehninger, A.L. Biochemistry (1980) [Pubmed]
  11. Basic calcium phosphate crystals stimulate the endocytotic activity of cells--inhibition by anti-calcification agents. Sun, Y., Zeng, X.R., Wenger, L., Cheung, H.S. Biochem. Biophys. Res. Commun. (2003) [Pubmed]
  12. Adsorption and mineralization effects of citrate and phosphocitrate on hydroxyapatite. Johnsson, M., Richardson, C.F., Sallis, J.D., Nancollas, G.H. Calcif. Tissue Int. (1991) [Pubmed]
  13. Basic calcium phosphate crystal induction of collagenase 1 and stromelysin expression is dependent on a p42/44 mitogen-activated protein kinase signal transduction pathway. Brogley, M.A., Cruz, M., Cheung, H.S. J. Cell. Physiol. (1999) [Pubmed]
  14. Calcium and disease: molecular determinants of calcium crystal deposition diseases. Misra, R.P. Cell. Mol. Life Sci. (2000) [Pubmed]
  15. A possible antiatherogenic role for phosphocitrate through modulation of low density lipoprotein uptake and degradation in aortic smooth muscle cells. Ward, L.C., Shankar, R., Sallis, J.D. Atherosclerosis (1987) [Pubmed]
  16. Evidence in vitro for an enzymatic synthesis of phosphocitrate. Moro, L., Stagni, N., Luxich, E., Sallis, J.D., de Bernard, B. Biochem. Biophys. Res. Commun. (1990) [Pubmed]
  17. The calcium-buffering phase of bone mineral: some clues to its form and formation. Neuman, M.W., Imai, K., Kawase, T., Saito, S. J. Bone Miner. Res. (1987) [Pubmed]
  18. Inhibition of basic calcium phosphate crystal-induced mitogenesis by phosphocitrate. Cheung, H.S., Sallis, J.D., Mitchell, P.G., Struve, J.A. Biochem. Biophys. Res. Commun. (1990) [Pubmed]
  19. Controlling influence of phosphocitrate in vitro and in vivo on calcium oxalate crystal formation and growth. Sallis, J.D., Parry, N.F., Meehan, J.D., Kamperman, H., Anderson, M.E. Scanning Microsc. (1995) [Pubmed]
  20. Basic calcium phosphate crystals up-regulate metalloproteinases but down-regulate tissue inhibitor of metalloproteinase-1 and -2 in human fibroblasts. Bai, G., Howell, D.S., Howard, G.A., Roos, B.A., Cheung, H.S. Osteoarthr. Cartil. (2001) [Pubmed]
  21. Scanning electron microscopy and molecular modeling of inhibition of calcium oxalate monohydrate crystal growth by citrate and phosphocitrate. Wierzbicki, A., Sikes, C.S., Sallis, J.D., Madura, J.D., Stevens, E.D., Martin, K.L. Calcif. Tissue Int. (1995) [Pubmed]
  22. Liposome and multiple emulsion formulations augment the anticalcifying efficacy of phosphocitrate in a cutaneous calcergy model. Kamperman, H., Sallis, J.D. J. Pharm. Pharmacol. (1995) [Pubmed]
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